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Used Chevrolet Silverado 1500 LT Trail Boss for Sale near Whitby, ON

76 results
Whitby, ON
2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD NewRoads Chrysler Dodge Jeep Ram

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

95,139 kilometres

$43,488

Good Deal
Newmarket, ON
48 km away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior colour:
White
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
95,139
Stock number:
28384P
VIN:
3GCPYFED5MG439461

Sponsored

2025 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

49,652 kilometres

$61,490

Fair Deal
Cobourg, ON
60 km away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Interior colour:
Black
Transmission:
Automatic
Mileage:
49,652
Stock number:
SG226062
VIN:
3GCUKFE85SG226062

Sponsored

2024 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

28,180 kilometres

$58,995

Fair Deal
Certified Pre-Owned
Orillia, ON
90 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior colour:
Gray
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
28,180
Stock number:
8564
VIN:
3GCUDFEDXRG182027

Sponsored

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

97,267 kilometres

$41,999

Great Deal
Brampton, ON
68 km away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior colour:
Black
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Interior colour:
Leather-Appointed Front Seats - Jet Black
Transmission:
Automatic
Mileage:
97,267
Stock number:
26355T1
VIN:
1GCPYFED5LZ299071

2024 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

97,424 kilometres

$48,899

Great Deal
Oakville, ON
72 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior colour:
White
Combined gas mileage:
10 L/100km
Fuel type:
Diesel
Interior colour:
Black
Transmission:
Automatic
Mileage:
97,424
Stock number:
196789
VIN:
3GCUDFE85RG196789

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2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

12,853 kilometres

$66,990

Good Deal
Certified Pre-Owned
Cobourg, ON
60 km away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Interior colour:
Black
Transmission:
Automatic
Mileage:
12,853
Stock number:
SG226133
VIN:
3GCUKFE82SG226133

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2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

33,028 kilometres

$59,990

Good Deal
Certified Pre-Owned
Cobourg, ON
60 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Black
Interior colour:
Black
Transmission:
Automatic
Mileage:
33,028
Stock number:
RG446702
VIN:
3GCUDFE82RG446702

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2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

28,811 kilometres

$64,990

Good Deal
Certified Pre-Owned
Cobourg, ON
60 km away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Red
Interior colour:
Black
Transmission:
Automatic
Mileage:
28,811
Stock number:
SG231569
VIN:
3GCUKFE89SG231569

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2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

13,608 kilometres

$62,978

Good Deal
Uxbridge, ON
28 km away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior colour:
Red
Combined gas mileage:
10 L/100km
Fuel type:
Diesel
Interior colour:
Black
Transmission:
Automatic
Mileage:
13,608
Stock number:
263724A
VIN:
3GCUKFE80SG259065

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2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

95,139 kilometres

$43,488

Good Deal
Newmarket, ON
48 km away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior colour:
White
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
95,139
Stock number:
28384P
VIN:
3GCPYFED5MG439461

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2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

26,895 kilometres

$46,818

Good Deal
Etobicoke, ON
56 km away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior colour:
Black
Combined gas mileage:
13 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
26,895
Stock number:
WGL1671A
VIN:
3GCPDFEK1NG551671

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2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

37,536 kilometres

$58,464

Good Deal
Certified Pre-Owned
Lindsay, ON
55 km away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Red
Interior colour:
Black
Transmission:
Automatic
Mileage:
37,536
Stock number:
11-260011A
VIN:
3GCUDFED0RG393110

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2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

114,011 kilometres

$39,950

Good Deal
Whitby, ON
3 km away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Combined gas mileage:
14 L/100km
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
114,011
Stock number:
41690X
VIN:
1GCPYFED3MZ431021

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2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

31,444 kilometres

$62,495

Fair Deal
Peterborough, ON
66 km away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior colour:
Gray
Transmission:
Automatic
Mileage:
31,444
Stock number:
SG313458
VIN:
3GCUKFE85SG313458

Sponsored

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